ūüďĆ Join the BPCrew Chapter in your city and meet up with more Yankees fans! ūüĎČ CLICK HERE

Re-drafting the Yankees in the 2000s

Have you ever looked back at the MLB draft results and wondered what could have been?

For every amazing selection (Derek Jeter #6 overall), there are countless picks that make you scratch your head, like the fact there were 24 players taken ahead of Mike Trout.

The baseball draft is unlike other sports. Today there are 40 rounds, which is fewer than there used to be (Mike Piazza was taken in the 62nd round – #1390 overall – in 1988). When you’re talking about that many players there are bound to be misses. But I still find it fun (and sometimes painful) to go back and re-draft the Yankees.

2000 Draft

Yankees 1st round pick (#28 overall): David Parrish, Catcher

The Yankees had good luck with Michigan Men when they drafted Parrish, who played in the minors until 2008 where he hit .241 overall. Believe it or not, he actually appeared on the Yankees’ major league roster in 2004 when Posada broke his nose in May. Parrish was depth behind John Flaherty but never got into a game.


— Adam Wainwright was taken by the Braves in the slot after the Yankees, #29 overall.

— Cliff Lee was taken in the 4th round by the Expos, who would eventually trade him to the Indians.

— Yadier Molina was taken in the 4th round by the Cardinals.

This is a good second guess because the Yankees took a catcher with their first pick. Molina turned into one of the best players from the 2000 draft and, like Parrish, came from a catching family — although Bengie and Jose had only been in the league a couple years to that point.

Yadi debuted at age 21 in 2004; I doubt the Yankees would have promoted him so quickly because they had Posada in his prime, but even if Molina came up a couple years later, Posada could have been able to extend his career by DH-ing more and catching less.
Embed from Getty Images

Maybe Lee was never meant to be a Yankee. And Molina would have been great, but the real second-guess is Wainwright, who made a name for himself in the Cardinals bullpen in 2006 and then developed into one of the best starters in the National League. He’s had his injury issues over the years but it sure would have been nice to have¬†Wainwright anchoring the Yankees rotation in the late-2000s.

Other notable picks include Edwin Encarnacion (9th round), James Shields (16th round), Jose Bautista (20th round), and Jason Bay (22nd round).

2001 Draft

Yankees 1st round pick (#23 overall):  John-Ford Griffin, Outfielder

The Yankees also had two picks in the supplemental first round, taking Infielder Bronson Sardinha (34th overall) and Pitcher Jon Skaggs (42nd overall).

Griffin was part of the trade that landed the Yankees Jeff Weaver. He wound up with Toronto where he played in parts of the 2005 and 2007 season.

Sardinha was a top-10 Yankees prospect in the mid-2000s and was a September call-up in 2007. He was even on the postseason roster, appearing in the infamous “bug game” as a 5th infielder. It was his last major league appearance.

Skaggs suffered injuries in the minors and never made it to the bigs.

The Yankees also drafted legend Shelly Duncan in the 2nd round this year.


— David Wright was taken 38th overall by the Mets, so the Yankees had two cracks at him.

It’s pretty easy to figure out this alternate reality: Wright replaces Aaron Boone after his injury in the 2003-04 off-season, which means the Yankees never acquire ARod. Some people will be happy by that and others will be upset.

Other notable picks include Dan Haren (2nd round), Ryan Howard (5th round), Kevin Youkilis (8th round), and Dan Uggla (11th round).

In looking at the rest of the first round and notable picks, Wright is the clear second-guess.

2002 Draft

The Yankees did not have a selection until the 5th round, and by that time you’re just throwing darts. They wound up with Matt Carson, who appeared in the majors with various teams from 2009 – 2013. Because there were no high-round picks, I’m not going to re-draft 2002.

2003 Draft

Yankees 1st round pick (#27 overall): Eric Duncan, Third Baseman

Duncan was a High School All-American but fizzled out in Triple-A.

Had the Yankees drafted Wright in 2001, they wouldn’t have had to take Duncan amirite?


— Adam Jones was drafted #37 overall by the Mariners, who would eventually trade him to the Orioles.

Other notable picks include Andre Ethier (2nd round), Jonathan Papelbon (4th round), and Matt Kemp (6th round).

As good as Jones was for Baltimore, this isn’t a massive second-guess like Wainwright and Wright are. And Papelbon would be our jackass if the Yankees drafted him.

2004 Draft

Yankees 1st round pick (#23 overall): Philip Hughes, Pitcher

Hughes is not a second-guess. Say what you will about Hughes, but he did contribute 182 games and 780.2 innings to the Yankees as a starter and reliever.

They also took Catcher Jonathan Poterson and Pitcher Jeffrey Marquez in the supplemental first round.

Poterson moved to the outfield and never rose above A-ball but Marquez was part of the trade to Chicago that returned the Yankees Nick Swisher, so that worked out in the end.


— Dustin Pedroia was drafted in the 2nd round by the Red Sox.

Embed from Getty Images

I know it’s hard to imagine Pedroia in pinstripes, and Cano was a better second baseman than him anyway, but it was a miss.

There were a few quality major leaguers taken in the first couple of rounds. Notable picks include Yovani Gallardo and Hunter Pence (2nd round), Wade Davis, Ian Desmond, and Adam Lind (3rd round), Chris Iannetta (4th round), and Ben Zobrist (6th round).

Take your pick from any of the above over Poterson.

2005 Draft

Yankees 1st round pick (#17 overall): C.J. Henry, Shortstop

I know you don’t draft for a position in baseball, but this is the first shortstop the Yankees took high in the draft so perhaps you could see Brian Cashman starting to think about post-Jeter plans. Henry ended up being traded to Philly for Bobby Abreu just a year later.

Brett Gardner was drafted in the 3rd round this year, which goes down as an excellent pick.


This draft had a lot of big names in the top-10 (Justin Upton, Alex Gordon, Ryan Zimmerman, Ryan Braun, Troy Tulowitzki and Andrew McCutchen) but I had a hard time finding a player after #17 that screams second-guess.

— Jacoby Ellsbury was picked #23 overall by the Red Sox.

Hear me out… If the Yankees drafted Ellsbury then that means they would not have paid him $153 million in free agency and we could have actually enjoyed Ells’ good years instead of his broken years.

Other notable picks include Chase Headley (2nd round) …. hahahaha… and Michael Brantley (7th round).

2006 Draft

Yankees 1st round pick (#21 overall): Ian Kennedy, Pitcher

This is also the year the Yanks took Joba Chamberlain in the supplemental first round.

I can’t say the Yankees were wrong on these players. I think they mishandled Joba, and Kennedy despite Kennedy being a Yankees bust, he is still pitching in the majors.


Usually you can find a diamond in the rough in the mid-to-late rounds but 2006 was pretty weak.

—¬†Adam Ottavino, drafted #30 overall by the Cardinals, would have fit right into the Yankees from day 1.

That’s the best I could come up with.

2007 Draft

Yankees 1st round pick (#30 overall): Andrew Brackman, Pitcher

Brackman, one of the Killer Bs, never materialized for the Yankees. Unlike 2006, this draft was loaded.


— Todd Frazier was drafted by the Reds in the supplemental first round. Did you know he’s from Toms River, NJ?

— Josh Donaldson was drafted by the Cubs in the supplemental first round.

— Giancarlo Stanton, known as Mike back then, was drafted by the Marlins in the 2nd round.

— Freddy Freeman was drafted by the Braves in the 2nd round.

— Jordan Zimmerman was drafted by the Nationals in the 2nd round.

Embed from Getty Images

Wow. Not only are all of those players good, they’re All-Stars.¬†Take your pick.

Unlike other years, the talent in the supplemental and 2nd round was just as good as the top of the draft, which featured David Price, Madison Bumgarner, Jason Heyward and Rick Porcello.

2008 Draft

Yankees 1st round pick (#28 overall): Gerrit Cole, Pitcher

The only reason Cole fell to the Yankees is because teams knew he was not going to sign. The Yankees thought money would change his mind. It did not. For that reason, let’s re-draft.


— Charlie Blackmon was drafted in the 2nd round by the Rockies.

It was the third time Blackmon was drafted. He was first taken out of high school in 2004 and then Junior College in 2005 (both times as a pitcher). When Colorado took him he was an outfielder, and has been ever since.

Other notable picks include Craig Kimbrel (3rd round) and Brandon Crawford (4th round), but Blackmon is my re-draft choice.

2009 Draft

Yankees 1st round pick (#29 overall): Slade Heathcott, Outfielder

I was actually really excited for Heathcott after this moment in 2015, but he never appeared in the majors after this season.


— James Paxton was drafted #37 overall by the Blue Jays but did not sign.

— Nolan Arenado was drafted by the Rockies in the 2nd round.

— DJ LeMahieu was drafted by the Cubs in the 2nd round.

Other notable picks include Kyle Seager (3rd round), Paul Goldschmidt (8th round) and Matt Carpenter (13th round).

How many amazing third baseman could the Yankees have drafted in the 2000s? Wright, Frazier, Donaldson, and Arenado all slipped through their fingers. As much as I love DJLM, Arenado is the clear miss here.

Mike Trout (#25 overall) was off the board by the time the Yankees took Heathcott. But that means 24 players were taken before him, and even the Angels took Randal Grichuk ahead of Trout.

How different would the Yankees look today had they made the right pick in just a couple of those drafts, never mind all of them?

But this blog was in no way bashing Cashman or the Yankees for missing. As I said at the top, drafting in baseball is extremely difficult. The road from the draft to the majors is a long one, and the rate of success for players is extremely low.